Water → Methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylate

HRID 1408865Notes

Reaction equation

HRID 1408865 reaction equation
[NH2:1][C:2]12[CH2:9][C:6]([C:10]([O:12][CH3:13])=[O:11])([CH2:7][CH2:8]1)[CH2:5][CH2:4][CH2:3]2.[CH3:14][C:15]1[N:20]=[C:19]([C:21](O)=[O:22])[CH:18]=[N:17][CH:16]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.O>C(Cl)Cl>[CH3:14][C:15]1[N:20]=[C:19]([C:21]([NH:1][C:2]23[CH2:9][C:6]([C:10]([O:12][CH3:13])=[O:11])([CH2:7][CH2:8]2)[CH2:5][CH2:4][CH2:3]3)=[O:22])[CH:18]=[N:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4708976-Methylpyrazine-2-carboxylic acidHCID 2724699PyBOPHCID 68048077Methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate

Product 1

HCID 68048079Methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 5-aminobicyclo[3.2.1]octane-1-carboxylate (0.98 g, 5.36 mmol) and 6-methylpyrazine-2-carboxylic acid (0.89 g, 6.45 mmol) in DCM (30 mL) and TEA (2 mL) was added PyBOP (3.35 g, 6.44 mmol). After stirring at room temperature overnight, water (30 mL) was added and the mixture was extracted with DCM (3×50 mL). The combined organic layer was washed with Sat. NaHCO3 (50 mL) and brine (50 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 1/1) to afford 1.28 g (79%) of methyl 5-(6-methylpyrazine-2-carboxamido)bicyclo[3.2.1]octane-1-carboxylate as an off-white solid. ESI-MS m/z: 304 (M+H)+.

Workup

  1. extractionthe mixture was extracted with DCM (3×50 mL)
  2. washThe combined organic layer was washed with Sat. NaHCO3 (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 1/1)

Sources & evidence

ORD record
ord-047823d033a44f1699b14b153abb83cd
Source dataset
uspto-grants-2014_12
Patent number
US08921370B2

Reaction notes

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